


Pickup Artist

by CLeighWrites



Series: SPN Kink Bingo 2020 [3]
Category: Supernatural
Genre: Bar Owner!Reader, Cunnilingus, F/M, Fellatio, Oral Sex, Plot What Plot/Porn Without Plot, Squirting, Supernatural Kink Bingo 2020, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-07-16
Updated: 2020-07-16
Packaged: 2021-03-05 03:14:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,167
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25187752
Author URL: https://archiveofourown.org/users/CLeighWrites/pseuds/CLeighWrites
Summary: The Winchesters walk into your bar… the rest is history
Relationships: Dean Winchester/You
Series: SPN Kink Bingo 2020 [3]
Series URL: https://archiveofourown.org/series/1615648
Comments: 4
Kudos: 35
Collections: SPN Kink Bingo 2020





	Pickup Artist

**Author's Note:**

> This was written for @ne-gans (Tumblr) Seven Deadly Sins challenge, my prompt was Pride. I also took the opportunity to fill the squirting square for my spn kink bingo card. Beta’d by the wonderous @deanwinchesterswitch (Tumblr)

It had been a Thursday night just like any other when a pair of tall, handsome men had strolled into your bar. They radiated power and prowess. They walked, in step, straight to the bar, sat down, then the one with the short hair gave you the nod that they were ready to order. 

You put the tiniest bit of bounce in your step so that your tits would move and stretch the already straining fabric of your tank top as you made your way to the other end of the bar. No sense in letting the night slip away without allowing yourself to have a little fun with a couple of large, attractive strangers. The man that had signaled you wasn’t shy about letting his eyes travel downward as you leaned against the bar. 

“What’ll it be, fellas?” 

“What’re you offerin’?” The captivating one with green eyes asked, the desire clear on his face. 

“Dean.” His buddy admonished.

“Come on, Sammy. Can’t mix a little business with pleasure?” 

You pursed your lips together as they had a silent battle with each other. “Why don’t we start with drinks and see where the night takes us?” you offered, trying to lighten their tense mood.

The green-eyed man, Dean, smiled back at you. “Sounds good to me, sweetheart. Two whiskeys, neat.” 

You nodded, then reached for two tumblers before shifting your hips to turn around and reach for the Jack. You knew that your tank would ride up your back, showing off your low-rider jeans and your tattoo. When you turned back to face the men, Dean had his head tilted and was licking his lips, while Sammy was quickly averting his eyes and nudging his friend when he caught him still staring at you. 

“See anything else you like?” you flirted while you poured out two fingers into each tumbler. 

“Damn right, I do,” Dean answered confidently. 

“You’ll have to forgive my brother,” Sammy started, “I swear we weren’t raised by wolves.”

“Speak for yourself, Sammy.” Dean winked at you as you handed over his drink.

“It’s ‘Sam’.” _Sam_ accepted his glass with a half-smile and a quick glance at your cleavage before staring into the amber depths. 

His bashfulness was adorable, especially coming from such a massive man, but a puppy wasn’t what you were in the mood for, a wolf on the other hand… 

“So, Sam, what brings you into town?” 

Dean bristled at being presumably sidelined and answered for his brother. “We’re in town for a case.”

The bartop creaked as you pulled your shoulders together--testing the strength of your tank top, and drawing both sets of eyes to you--then leaned forward a bit more. “Oh, what kind of case? Are you feds?” Then a thought occurred to you, taking you out of the flirty mindset you had been in. “Are you here about the serial killer?”

Sam failed at hiding a flinch. “What serial killer?” His voice was hard and much more assertive than his previous reaction would have led you to believe him capable of. 

Darting your eyes around the room, making sure the Thursday night slump was still in progress, you lowered your voice and answered. “Those three women that were murdered. All had long brown hair, all were recently separated from their husbands, and all of them were found in the woods-” you couldn’t bring yourself to finish your thought. 

Dean cleared his throat before he responded. “Nope,” he popped the ‘p’, “haven’t heard anything about it.” He took a conspicuous sip of his whiskey and avoided eye contact. 

Sam, for his part, kept his features schooled. “Sounds terrible. I hope they catch ‘em before they kill someone else.”

You didn’t buy what they were selling one bit, but you figured that they probably couldn’t talk about an ongoing investigation, so you let them off the hook. “Mmhmm, _anyways_. Anything else I can get for you?”

Sam smiled and shook his head while Dean licked the whiskey off of his lips. He must have one hell of an oral fixation. His lips looked like they could do some phenomenal damage, in the absolutely best way possible. Pain on your lip brought you back to the present, and Dean was smirking at you like he knew exactly where your mind had gone. You released your lip but let your gaze drift. 

“You see something _you_ like, honey?” He was a cocky one, but had every right to be, looking the way he did. 

It had been your experience that the cockiest of the pretty boys, didn’t try very hard in the sack. Unfortunately for all of them, their looks only did so much in the ‘getting you off’ department. After a very enlightening article that blasted Bradley Cooper’s bedroom skills, you’d almost quit going after the pretty boys. Sure they made good bait, but they would just give up after that. You liked a man that knew what to do with your body once he got access to it. 

“Yeah, you do.” He winked again. This was going to, hopefully, be a very good night. 

****

Sam left around midnight, and Dean stayed, making snide remarks as men tried and failed to make you blush the way he had been able to, which was a feat in and of itself. Since the last person had left, you had shut the overhead speakers off and busied yourself with cleaning the few remaining glasses from your sink. It wouldn’t be too much longer before you could lock up and see what all this gorgeous man was capable of.

“You’ve been talking yourself up all night. I hope you haven’t been exaggerating.” 

“Oh, Y/N, I’ve been downplaying what all I’m going to do to you… as soon as you lock up this bar, you’ll find out firsthand.”

The laugh you let loose echoed in the empty room. “You sure do talk a big game.”

“There’s no shame in advertising my abilities. Offering my services to those in,” Dean licked his lips, yet again, his eyes traveling the length of your body, “need.”

“You know,” you leaned against the bar and arched your back, “pride is one of the seven deadly sins.” 

Dean mumbled something into his glass that sounded like, ‘Pride couldn’t kill me if he’d wanted to’, which was such a funny thing to say that you couldn’t control your laugh. 

“Listen; if there’s one thing I can be proud of, it’s my ability to satisfy.”

You quirked an eyebrow at his hubris. “Oh, really?”

In lieu of an answer, he lifted his tumbler, winked, then drained the rest of the glass. You couldn’t help but notice how his fingers and lips curled around the rim, the way his throat contracted as he swallowed. He was a fine specimen of a man. When he caught you staring, and possibly drooling, he raised his eyebrows and rotated on his stool to look around the empty barroom. 

“Isn’t it about closing time?”

You glanced at the clock above the door and found that it was about a quarter till two. Another look around the room confirmed that Dean was the last patron of the night. The thought of what you were about to do made your blood rush with anticipation and nerves. You had never been one to have sex with every tempting stranger that walked into your bar. Still, it had been a while, and Dean’s boastful proclamations of his sexual prowess were intriguing enough for you to indulge yourself.

A flirtatious smile spread across your face as you reached out and dinged your service bell. “Last call!” Dean laughed, and it was a gorgeous sight. “So, what’ll it be?” you asked as you backed away from him to move around the bar without taking your eyes off of him. 

His body turned, following you like a sunflower follows the sun. “I have a pretty good idea of what I want to get next. But I’m not ready to put my order in quite yet.”

“Oh?” You were halfway across the room, heading toward the entry to lock the front doors. “Well, I hate to tell you this,” you reached the door and put your hand on the lock, “but once I lock up for the night, I don’t pour any more drinks.”

“It’s not that kinda drink that I’m looking for, darlin’.” He started taking very deliberate steps toward you, like an animal waiting to pounce. 

The click of the lock securing the door barely had time to reach his ears before he was on you. One hand on your hip, the other in your hair as he slammed you into the door and claimed your mouth with his own. You opened to him immediately, the smell and taste of whiskey invading your senses. 

The press of his lips on yours and the sure pressure of his tongue in your mouth was just as intoxicating as the spirits you sold for a living. His hand traveled from your hip to your thigh, and when he applied some pressure, you took your cue and jumped, wrapping your legs around his waist. He easily carried you across the room, back to the bar, where he sat you on the edge, then shoved the two nearest stools out of his way. 

The new position made you a head taller than him, putting his face directly in front of your chest. He showed no hesitation as he shoved both hands up your tank top, bunching the thin material over your breasts and pulling the cups of your bra down under them in one swift move. The artificial air combined with your spiked arousal to harden your nipples instantly. His lips latched onto your left nipple, and his fingers pinched and pulled at your right. 

While he ravaged your tits, his right hand teased its way down your side, then under your waistband, around to the button. He pulled back long enough to make eye contact with you, his question endearing, and unasked; you nodded your head in permission, then he carried on with his course of action. With a flick of his fingers, he undid your pants. Then, just as quickly, his hand worked its way under the band of your panties, fingers teasing down toward your clit. The man was a master.

In less than five minutes, Dean had turned you into a moaning mess on your bartop. After pulling your top the rest of the way over your head, and removing your bra, he moved his attention to your neck, making your toes curl as he attended to a particular place behind your ear. He hadn’t even gotten your pants off yet, and he was already proving that his claims were justified. 

You came on his fingers before he had you lean back on shaky arms to lift your hips so that he could remove your shoes, jeans, and panties. The bartop was warm and smooth under your bare ass. After tossing your pants off to the side, he pulled you to the edge of the bar, spread your legs wide, and licked his way over your sex to your clit then sucked hard. 

He kept your bud between his lips and flicked his tongue over your sensitive nerves until you couldn’t hold yourself up any longer. Without removing his face from between your legs, he turned your hips so that you could lean back onto the bar, then went back to work, eating you alive. The pornographic sounds of him slurping and lapping at your wet pussy rang throughout the empty bar, propelling you toward your second orgasm of the night. Just as your legs began to shake, he latched onto your clit and shook his head, burying his face deeper into you. He shoved two fingers into your dripping pussy, then growled, sending vibrations deep into your core. Overstimulation shattered any resistance your body was clinging to, and you gushed your release all over his face.

His mouth never stopped working you while you convulsed through your explosive orgasm. The obscene squelch of him lapping up your juices was enough to prolong your pleasure. That was the first time you had ever squirted for a stranger; Dean had definitely not exaggerated his expertise. On that same note, neither had you. Although you were still shaky, it was time to return the favor. 

Dean turned out to be an actual gentleman, not only had he gotten you off first--twice--but he helped you down from the bar as well; he even kept a firm hand on your shoulder while you got your footing. Your clit was still tingling from the attention he had just given you, and your mouth watered at the chance to repay him. 

With shaky fingers, you undid his belt buckle, unbuttoned, and unzipped his pants, then pulled them down to his ankles. You couldn’t be bothered to take his boots off, so you ushered him to sit on the nearest stool and to lean back against the bar. Only sparing a moment to take in his exposed appearance, you grabbed hold of him at the base and squeezed while you leaned in to taste yourself from his lips. It’s the wettest, most depraved kiss you’d ever shared with anyone, and it had you aching all over again. 

As soon as you pried your lips from his, you took him all the way into your mouth. There was no sense in teasing him; no time for gentle kitten licks around the tip or licking him from the balls up, so you took him in until your gag reflex tried to kick in. Working through the initial reflex, you built up a steady pattern, effortlessly alternating between suction and movement, and using your hands to massage and squeeze his balls and gripping him at the base, cutting off his circulation. 

His hands were in your hair, sometimes pulling the strands, while other times just offering a firm pressure. His breathing was becoming erratic, and his moans were confirming the existence of a higher power. You were dripping wet, only from having the weight of his cock in your mouth and hearing all the different, needy noises you were pulling from him. You knew that you were good at sucking dick, but the sounds that he was making were better than you could have imagined.

A more insistent pull on your hair had you sucking your way off of his dick and batting your eyelashes innocently while you held eye contact. You knew he was about to blow his load, and you were more than willing to have him fuck you until he came. More than ever, you were glad that you had gotten an IUD implant, no more worrying about having to remember if you took a pill. 

“Damn, darlin’, you weren’t kidding about only needing five minutes.” He closed his eyes and shook his head, replacing your hand with his own around his cock in order to keep you from stroking him anymore.

“I told you,” you sassed back, before pecking him on the lips.

He chased you for more with his eyes closed until he realized you were pulling away. His eyes went wide, a momentary look of worry ghosting his face before he understood what you were doing. With your arms crossed on the edge of the bar, you arched your back and presented yourself to him. You had never seen a man kick his shoes and pants off so fast. 

Your laugh abruptly cut off when one of his hands grabbed your hip, angling you toward his cock, held steady in his other. The stretch of him filling you up was almost too much after everything else your cunt had been subjected to, but it was a pleasurable pain. As wet as you were, he slid in as deep as he was able to in one smooth thrust. Your twin moans danced their way through the open space. 

It only took him a moment to collect himself before he started fucking into you without restraint. You braced yourself against the bar with your arms and arched your back more to get him to hit you in all the right places. The thick drag of his cock against your ravaged sex was building you back up toward another world-tilting orgasm. His grip on your hips tightened, then one of his hands worked its way forward around your thigh so that his fingers could reach where your bodies connected. Once he started stroking furiously at your clit, your knees gave out. He was simultaneously fucking you, holding you up, and rubbing you off while you desperately clung to the bar. 

If you had been able to concentrate, you would have noticed that you had come twice, back to back. As it were, you were only aware of the massive sploosh that soaked Dean’s cock, and both of your thighs, before dripping down to the floor. Dean griped you with both hands again and fucked you more persistently after that, his groans becoming desperate pleas as his hips started to falter. After a few more stilted thrusts, he shoved in deep, grunting through his release. His pulsing cock filled you up while your body milked him for everything he had to give. 

When he slipped himself from you, you both giggled breathlessly at the overstimulation. Dean backed himself onto a stool, then pulled you to rest between his legs and against his chest. Once you had both recovered from your, almost literally, mind-blowing orgasms, you pulled yourself out of the comfort of his arms. 

“Well, your arrogance didn’t come from nowhere,” you substantiate while you look for all of your clothes. 

“You weren’t so bad yourself.” Dean caught his pants and played with them before stepping into them. “You know, we’re gonna be in town-”

“Dean,” you interrupted. “Don’t feel like you have to say something, or even come back and see me again. This was fun, right?”

“Yeah, I’d say.”

“Okay, then don’t make this awkward. If you want to come back in for a drink… or whatever; that’s cool. If not, tonight was a really great time.”

“Understood.” He laughed a little to himself. “You know, I think that’s the first time I’ve ever been given ‘the talk’. It’s usually me letting ‘em down easy.”

“Aww, you think this is my first time picking up a patron?”

Dean sputtered. “You… picked… me… what?”

Finally dressed, you patted him on the cheek. “You’re adorable when you’re all flustered.” You smacked him on the ass on your way behind the bar to count the register and start closing down. “You don’t have to worry about locking it on your way out, I’ve got a shotgun in case anyone sketchy comes in.”

Dean stood there for a long moment before he made his way to the door. “It was great meeting you, Y/N; stay cool.”

“You, too, Dean.”

**Author's Note:**

> Thanks for reading! Don't be shy, let me know what you think!


End file.
